2-[1'-(p-methoxyphenyl)-2'-nitroethyl]-1,3-diphenylpropane-1,3-dione | 1134099-91-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-[1'-(p-methoxyphenyl)-2'-nitroethyl]-1,3-diphenylpropane-1,3-dione
• 英文别名: (S)-2-(1-(4-methoxyphenyl)-2-nitroethyl)-1,3-diphenylpropane-1,3-dione；2-[(1S)-1-(4-methoxyphenyl)-2-nitroethyl]-1,3-diphenylpropane-1,3-dione
• CAS: 1134099-91-4
• 化学式: C₂₄H₂₁NO₅
• 分子量: 403.434
• InChiKey: QCKGDJYUBDKHLG-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-甲氧苯基)-2-硝基乙烯 、 二苯甲酰基甲烷 在 9-amino-(9-deoxy)-epi-quinine 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以92%的产率得到2-[1'-(p-methoxyphenyl)-2'-nitroethyl]-1,3-diphenylpropane-1,3-dione
  参考文献：
  名称：

  Recyclable organocatalysis: highly enantioselective Michael addition of1,3-diaryl-1,3-propanedioneto nitroolefins

  摘要：

  首次报道了使用一种简单的有机催化剂进行1,3-二芳基-1,3-丙二酮与硝基烯烃的Michael加成反应，该反应获得了优异的产率（81-97%）和高度的对映选择性（90%到>99%的ee值）；催化剂和过量的反应物可通过简单的过滤操作重复使用七次。

  DOI：

  10.1039/b813915f

文献信息

• Modularly Evolved 2-AminoDMAP/Squaramides as Highly Active Bifunctional Organocatalysts in Michael Addition
  作者：Murat Işık、M. Yagiz Unver、Cihangir Tanyeli

  DOI：10.1021/jo5022597

  日期：2015.1.16

  We report a new family of chiral bifunctional acid/base type organocatalysts, 2-aminoDMAP/Squaramides, which are proved to be highly active (1 mol % cat. loading) promoters in conjugate addition of dibenzoylmethane to various trans-β-nitroalkenes. Steric demand of the catalysts was clearly seen by a set-by-set modulation of the squaramide unit through electronic and steric factors. The synergistic

  我们报道了一个新的手性双官能酸/碱型有机催化剂，2-aminoDMAP / Squaramides家族，被证明是在将二苯甲酰甲烷共轭加成到各种反式-β-硝基烯烃中的高活性（1 mol％催化剂负载量）促进剂。通过电子和空间因素对方酰胺单元进行逐组调节，可以清楚地看到催化剂的立体需求。2-氨基DMAP“超强碱”与空间受限的方酰胺（氢键供体）的协同作用，使得在短短几个小时内即可将一系列反应物完全转化为相应的迈克尔加成物，且选择性极高（ee高达98％）。
• Synthesis of Chiral Tertiary Amine–Thioureas Based on Spirobi­indane and Application in Catalytic Asymmetric Michael Addition Reaction
  作者：Zhao Han、Xufeng Lin

  DOI：10.1055/s-0039-1691643

  日期：2020.4

  A series of novel chiral bifunctional tertiary amine–thioureas based on spirobiindane were designed and synthesized as organo­catalysts. One of these catalysts was shown to promote the asymmetric Michael addition reaction of 1,3-diphenylpropane-1,3-dione to nitro­olefins, affording the desired products in good yields (up to 95%) and enantioselectivities (up to 98% ee).

  设计并合成了一系列基于螺双茚满的新型手性双官能叔胺-硫脲作为有机催化剂。这些催化剂之一显示出可以促进1,3-二苯丙烷-1,3-二酮与硝基烯烃的不对称迈克尔加成反应，从而以高收率（高达95％）和对映选择性（高达98％ee）提供所需的产物。 。
• Novel carbohydrate-based thioureas as organocatalysts for asymmetric michael addition of 1,3-dicarbonyl compounds to nitroolefins
  作者：Róbert Rončák、Monika Tvrdoňová、Jozef Gonda、Ján Elečko

  DOI：10.1016/j.tet.2020.131339

  日期：2020.7

  A series of novel carbohydrate-derived thioureas were synthesized and examined as catalysts for the asymmetric Michael addition of symmetrical 1,3-dicarbonyl compounds, including dimethyl malonate, to several trans-β-nitrostyrenes. High enantioselectivities (up to 94% ee) as well as high yields (up to 98%) were attained using a bifunctional organocatalyst bearing a cinchona-based alkaloid unit.

  一系列新颖的碳水化合物衍生的硫脲的合成和研究作为催化剂用于不对称迈克尔加成对称1,3-二羰基化合物，包括丙二酸二甲酯，对几个反式- β -nitrostyrenes。使用带有金鸡纳生物碱单元的双功能有机催化剂，可以获得高对映选择性（最高94％ee）和高产率（最高98％）。
• MICHAEL REACTION WITH RECOVERY OF THE CATALYST
  申请人：ZHONG GUOFU

  公开号：US20120004424A1

  公开（公告）日：2012-01-05

  Disclosed is a process of carrying out a Michael reaction with recovery of the catalyst, where a compound of formula (1): is reacted with a compound of formula (2): in the presence of a catalyst of formula (4): where the compounds of formulae (1) and (2) undergo a Michael reaction.

  揭示了一种进行Michael加成反应并回收催化剂的过程，其中式（1）的化合物与式（2）的化合物在式（4）的催化剂存在下发生Michael反应。
• Highly enantioselective Michael addition of 1,3-dicarbonyl compounds to nitroalkenes catalyzed by designer chiral BINOL–quinine–squaramide: efficient access to optically active nitro-alkanes and their isoxazole derivatives
  作者：Bin Liu、Xin Han、Ze Dong、Hao Lv、Hai-Bing Zhou、Chune Dong

  DOI：10.1016/j.tetasy.2013.08.010

  日期：2013.10

  A chiral BINOL-quinine-squaramide has been identified as the best catalyst for the asymmetric Michael addition of nitroalkenes to 1,3-dicarbonyl compounds. A series of chiral nitroalkanes were prepared with approximately >99% ee. Furthermore, the methodology was applied successfully to the synthesis of enantiomerically pure isoxazoles derivatives (>99% ee). (C) 2013 Elsevier Ltd. All rights reserved.